catena-Poly[[[bis­(thio­urea-κS)copper(I)]-μ-thio­urea-κ²S:S] iodide acetonitrile hemisolvate]

The title complex, {[Cu(CH₄N₂S)₃]I·0.5CH₃CN}_n, was formed by the reaction of CuI and thio­urea in acetonitrile. There are two independent Cu^I ions in the asymmetric unit which are coordinated by two terminal and two bridging thio­urea ligands to form a one-dimensional helical chain structure progagating in the a-axis direction. Each Cu^I ion is in a distorted tetra­hedral coordination environment. The crystal structure is stabilized by weak N—H...S and N—H...I hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.016 Å
• R factor = 0.034
• wR factor = 0.078
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Cu1    -   S1      ..      12.36 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Cu1    -   S6_b    ..      12.88 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Cu2    -   S6      ..      19.45 su

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.269     0.360
            Tmin and Tmax expected:      0.185     0.277
            RR =      1.121
            Please check that your absorption correction is appropriate.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.13
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.77
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu2    -   S1      ..       5.20 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu2    -   S5      ..       7.92 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         C7
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         16
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2A    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3B    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H4A    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N6     -   H6B    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N9     -   H9A    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N10    -   H10B   ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A    ..  I2      ..       3.14 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B    ..  S5      ..       2.96 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B    ..  I1      ..       3.17 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A    ..  I2      ..       3.11 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A    ..  I1      ..       3.22 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5A    ..  I2      ..       3.32 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A    ..  I2      ..       3.12 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A    ..  S2      ..       2.89 Ang.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.770
            Tmax scaled      0.277 Tmin scaled      0.207
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.03
           From the CIF: _reflns_number_total               4963
           Count of symmetry unique reflns         2829
           Completeness (_total/calc)            175.43%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2134
           Fraction of Friedel pairs measured     0.754
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  27 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  14 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

Some copper(I) compounds containing thiourea ligands have been described previously (Bombicz et al., 2004; Bott et al., 1998; Stocker et al., 1996). In this paper, we report the synthesis and the structure of a complex formed by the reaction of thiourea with cuprous iodide. The asymmetric unit of the title compound is shown in Fig. 1. The Cu^I ions have distorted tetrahedral coordination geometries formed by two bridging thiourea ligands and two terminal thiourea ligands. A one-dimensional helical chain structure parallel to the a axis direction is formed (Fig. 2). An iodide counter ion and half an acetonitrile solvent molecule complete the formula unit although there are two formula units in the asymmetric unit of the crystal structure. The Cu—S distances are in the range of 2.275 (2)–2.435 (2) Å, and agree with those in related structures (Bombicz et al., 2004). In the title compound, the S=C distances are the same within experimental error.

In the crystal structure, there are two different types of hydrogen bonds. Intramolecular N—H···S interactions appear to influence the conformation of the helical chains while intermolecular N—H···S and N—H···I interactions stabilize the crystal structure.

Related literature

For related literature, see: Bombicz et al. (2004); Bott et al. (1998); Stocker et al. (1996).

S2. Experimental

CuI (0.19 g 1 mmol) and thiourea (0.16 g 2 mmol) in 10 ml acetonitrile were refluxed for 24 h, forming a colorless solution. After filtration, the solution was allowed to evaporate slowly and crystals suitable for X-ray diffraction were obtained after several days.

S3. Refinement

All H atoms were placed geometrically and treated as riding on their parent atoms, with, N—H 0.86, C—H 0.96 Å, with U_iso(H) = 1.2U_eq(N), U_iso(H) = 1.5U_eq(C).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenberg & Berndt, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. The asymmetric unit with atom labels and 30% probability displacement ellipsoids. H atoms are not shown.
	Fig. 2. Part of the one-dimensional helical chain structure of the title complex.

catena-Poly[[[bis(thiourea-κS)copper(I)]-µ-thiourea-κ²S:S] iodide acetonitrile hemisolvate]

Crystal data

[Cu(CH4N2S)3]I·0.5C2H3N	F(000) = 1704
Mr = 439.33	Dx = 2.055 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6067 reflections
a = 13.392 (8) Å	θ = 2.4–24.6°
b = 13.874 (9) Å	µ = 4.14 mm^−1
c = 15.289 (9) Å	T = 298 K
V = 2841 (3) Å^3	Block, colorless
Z = 8	0.43 × 0.39 × 0.31 mm

Data collection

Bruker SMART CCD diffractometer	4963 independent reflections
Radiation source: fine-focus sealed tube	4175 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
ϕ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.269, Tmax = 0.360	k = −14→16
14883 measured reflections	l = −18→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0355P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
4963 reflections	Δρmax = 0.75 e Å^−3
280 parameters	Δρmin = −0.56 e Å^−3
0 restraints	Absolute structure: Flack (1983), 2149 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (2)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.43289 (6)	0.62730 (6)	0.51306 (5)	0.0352 (2)
Cu2	0.21551 (6)	0.78050 (6)	0.36342 (6)	0.0378 (2)
I1	0.73774 (3)	0.35628 (3)	0.66369 (3)	0.03691 (12)
I2	0.56899 (4)	0.12983 (4)	0.53537 (3)	0.04740 (14)
N1	0.5123 (4)	0.8657 (5)	0.4926 (4)	0.0528 (18)
H1A	0.5402	0.9200	0.5043	0.063*
H1B	0.5389	0.8129	0.5106	0.063*
N2	0.3902 (5)	0.9446 (5)	0.4202 (5)	0.064 (2)
H2A	0.4189	0.9984	0.4325	0.077*
H2B	0.3358	0.9442	0.3903	0.077*
N3	0.3841 (5)	0.3114 (4)	0.4764 (4)	0.0459 (16)
H3A	0.4073	0.2612	0.5024	0.055*
H3B	0.3327	0.3064	0.4430	0.055*
N4	0.5048 (5)	0.3993 (5)	0.5388 (4)	0.0566 (19)
H4A	0.5263	0.3479	0.5640	0.068*
H4B	0.5345	0.4534	0.5474	0.068*
N5	0.2276 (5)	0.5314 (6)	0.6094 (5)	0.067 (2)
H5A	0.1708	0.5049	0.6202	0.081*
H5B	0.2535	0.5267	0.5581	0.081*
N6	0.2313 (5)	0.5839 (5)	0.7483 (4)	0.0615 (19)
H6A	0.1745	0.5566	0.7571	0.074*
H6B	0.2602	0.6146	0.7901	0.074*
N7	−0.0075 (5)	0.5530 (5)	0.2887 (5)	0.057 (2)
H7A	−0.0649	0.5543	0.2634	0.068*
H7B	0.0118	0.5018	0.3154	0.068*
N8	0.0191 (4)	0.7058 (4)	0.2453 (4)	0.0462 (17)
H8A	−0.0385	0.7056	0.2204	0.055*
H8B	0.0561	0.7564	0.2431	0.055*
N9	0.2578 (5)	0.7295 (5)	0.1506 (4)	0.0568 (18)
H9A	0.2765	0.7019	0.1030	0.068*
H9B	0.2487	0.6959	0.1972	0.068*
N10	0.2579 (7)	0.8700 (6)	0.0790 (4)	0.089 (3)
H10A	0.2767	0.8410	0.0321	0.107*
H10B	0.2486	0.9314	0.0786	0.107*
N11	0.1163 (4)	0.9243 (5)	0.6331 (4)	0.0478 (16)
H11A	0.1405	0.9268	0.6851	0.057*
H11B	0.0637	0.9570	0.6201	0.057*
N12	0.2399 (5)	0.8212 (5)	0.5951 (4)	0.065 (2)
H12A	0.2631	0.8245	0.6474	0.078*
H12B	0.2691	0.7856	0.5568	0.078*
N13	0.4435 (6)	0.5766 (7)	0.2168 (5)	0.080 (3)
S1	0.37489 (12)	0.75471 (12)	0.42179 (11)	0.0289 (4)
S2	0.38359 (13)	0.49427 (13)	0.43325 (11)	0.0347 (4)
S3	0.38436 (12)	0.63528 (15)	0.65547 (11)	0.0409 (4)
S4	0.16498 (11)	0.62484 (13)	0.33684 (12)	0.0377 (4)
S5	0.20735 (14)	0.88344 (13)	0.24281 (11)	0.0407 (4)
S6	0.11161 (11)	0.86565 (13)	0.46883 (10)	0.0300 (3)
C1	0.4293 (5)	0.8635 (5)	0.4470 (4)	0.0371 (16)
C2	0.4269 (5)	0.3951 (5)	0.4876 (4)	0.0351 (16)
C3	0.2741 (5)	0.5786 (5)	0.6706 (5)	0.0375 (16)
C4	0.0505 (4)	0.6292 (5)	0.2864 (4)	0.0339 (15)
C5	0.2434 (5)	0.8202 (6)	0.1521 (4)	0.0462 (19)
C6	0.1593 (4)	0.8707 (5)	0.5735 (4)	0.0306 (14)
C7	0.4660 (6)	0.6535 (9)	0.2169 (5)	0.060 (3)
C8	0.4976 (7)	0.7529 (7)	0.2179 (7)	0.075 (3)
H8C	0.4444	0.7925	0.2398	0.112*
H8D	0.5143	0.7728	0.1595	0.112*
H8E	0.5551	0.7595	0.2549	0.112*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0331 (4)	0.0335 (5)	0.0391 (5)	−0.0031 (4)	0.0053 (4)	−0.0024 (4)
Cu2	0.0300 (4)	0.0451 (5)	0.0383 (5)	−0.0036 (4)	−0.0070 (4)	−0.0002 (4)
I1	0.0318 (2)	0.0460 (3)	0.0330 (2)	−0.0026 (2)	0.00101 (19)	−0.0021 (2)
I2	0.0590 (3)	0.0338 (3)	0.0494 (3)	0.0017 (3)	0.0004 (2)	0.0003 (3)
N1	0.041 (3)	0.030 (3)	0.087 (5)	−0.005 (3)	−0.032 (3)	−0.001 (4)
N2	0.049 (4)	0.033 (4)	0.110 (6)	−0.015 (3)	−0.035 (4)	0.013 (4)
N3	0.052 (4)	0.039 (4)	0.047 (4)	−0.001 (3)	−0.006 (3)	0.003 (3)
N4	0.060 (5)	0.043 (4)	0.067 (5)	−0.004 (3)	−0.033 (4)	0.013 (4)
N5	0.042 (4)	0.082 (5)	0.078 (5)	−0.022 (4)	0.012 (4)	−0.004 (4)
N6	0.067 (5)	0.062 (4)	0.055 (4)	−0.004 (4)	0.032 (4)	0.006 (3)
N7	0.047 (4)	0.037 (4)	0.087 (5)	−0.008 (3)	−0.012 (4)	0.008 (4)
N8	0.024 (3)	0.042 (4)	0.072 (5)	0.000 (3)	−0.012 (3)	0.004 (4)
N9	0.058 (4)	0.072 (5)	0.041 (4)	0.015 (4)	0.011 (3)	−0.018 (3)
N10	0.146 (8)	0.089 (6)	0.032 (4)	−0.057 (7)	0.019 (5)	−0.008 (4)
N11	0.042 (3)	0.069 (5)	0.032 (3)	0.018 (3)	−0.006 (3)	−0.016 (3)
N12	0.049 (4)	0.117 (6)	0.028 (3)	0.039 (4)	−0.005 (3)	−0.004 (3)
N13	0.066 (5)	0.106 (7)	0.066 (5)	−0.018 (5)	−0.025 (4)	0.011 (5)
S1	0.0239 (8)	0.0303 (9)	0.0326 (9)	0.0005 (7)	−0.0038 (7)	0.0001 (7)
S2	0.0379 (9)	0.0327 (10)	0.0336 (10)	−0.0020 (8)	−0.0104 (8)	0.0010 (8)
S3	0.0372 (8)	0.0529 (11)	0.0327 (9)	−0.0054 (9)	0.0030 (8)	−0.0016 (9)
S4	0.0291 (8)	0.0365 (10)	0.0474 (10)	0.0026 (7)	−0.0061 (8)	0.0006 (9)
S5	0.0527 (11)	0.0376 (10)	0.0319 (9)	0.0019 (8)	−0.0045 (8)	0.0017 (8)
S6	0.0214 (7)	0.0422 (10)	0.0265 (8)	0.0012 (8)	0.0006 (6)	−0.0039 (9)
C1	0.035 (3)	0.035 (4)	0.042 (4)	0.003 (4)	−0.004 (3)	0.001 (3)
C2	0.032 (4)	0.042 (4)	0.031 (4)	−0.009 (3)	−0.003 (3)	−0.004 (3)
C3	0.038 (4)	0.032 (4)	0.042 (4)	0.007 (3)	0.010 (4)	0.008 (3)
C4	0.030 (3)	0.034 (4)	0.038 (4)	0.001 (3)	0.003 (3)	−0.004 (3)
C5	0.037 (4)	0.068 (6)	0.034 (4)	−0.011 (4)	−0.003 (4)	−0.003 (4)
C6	0.025 (3)	0.042 (4)	0.025 (3)	−0.003 (3)	−0.001 (3)	0.003 (3)
C7	0.040 (5)	0.100 (9)	0.041 (5)	−0.003 (5)	0.000 (4)	0.012 (5)
C8	0.059 (6)	0.096 (8)	0.069 (7)	−0.013 (5)	0.028 (5)	0.000 (6)

Geometric parameters (Å, º)

Cu1—S3	2.275 (2)	N7—H7B	0.8600
Cu1—S2	2.309 (2)	N8—C4	1.303 (9)
Cu1—S1	2.382 (2)	N8—H8A	0.8600
Cu1—S6^i	2.411 (2)	N8—H8B	0.8600
Cu2—S4	2.299 (2)	N9—C5	1.273 (10)
Cu2—S5	2.335 (2)	N9—H9A	0.8600
Cu2—S1	2.341 (2)	N9—H9B	0.8600
Cu2—S6	2.435 (2)	N10—C5	1.328 (10)
N1—C1	1.313 (8)	N10—H10A	0.8600
N1—H1A	0.8600	N10—H10B	0.8600
N1—H1B	0.8600	N11—C6	1.309 (8)
N2—C1	1.307 (9)	N11—H11A	0.8600
N2—H2A	0.8600	N11—H11B	0.8600
N2—H2B	0.8600	N12—C6	1.321 (9)
N3—C2	1.307 (8)	N12—H12A	0.8600
N3—H3A	0.8600	N12—H12B	0.8600
N3—H3B	0.8600	N13—C7	1.109 (12)
N4—C2	1.306 (8)	S1—C1	1.719 (7)
N4—H4A	0.8600	S2—C2	1.708 (7)
N4—H4B	0.8600	S3—C3	1.689 (7)
N5—C3	1.301 (10)	S4—C4	1.718 (6)
N5—H5A	0.8600	S5—C5	1.711 (8)
N5—H5B	0.8600	S6—C6	1.725 (6)
N6—C3	1.321 (9)	S6—Cu1^ii	2.411 (2)
N6—H6A	0.8600	C7—C8	1.442 (14)
N6—H6B	0.8600	C8—H8C	0.9600
N7—C4	1.313 (8)	C8—H8D	0.9600
N7—H7A	0.8600	C8—H8E	0.9600
S3—Cu1—S2	117.58 (8)	C6—N11—H11A	120.0
S3—Cu1—S1	115.55 (8)	C6—N11—H11B	120.0
S2—Cu1—S1	100.97 (8)	H11A—N11—H11B	120.0
S3—Cu1—S6^i	99.89 (6)	C6—N12—H12A	120.0
S2—Cu1—S6^i	112.14 (7)	C6—N12—H12B	120.0
S1—Cu1—S6^i	111.15 (7)	H12A—N12—H12B	120.0
S4—Cu2—S5	114.90 (8)	C1—S1—Cu2	109.7 (2)
S4—Cu2—S1	101.08 (7)	C1—S1—Cu1	112.4 (2)
S5—Cu2—S1	115.93 (7)	Cu2—S1—Cu1	129.34 (8)
S4—Cu2—S6	113.86 (7)	C2—S2—Cu1	106.8 (2)
S5—Cu2—S6	101.49 (8)	C3—S3—Cu1	111.0 (3)
S1—Cu2—S6	110.05 (7)	C4—S4—Cu2	108.0 (3)
C1—N1—H1A	120.0	C5—S5—Cu2	108.3 (3)
C1—N1—H1B	120.0	C6—S6—Cu1^ii	105.0 (2)
H1A—N1—H1B	120.0	C6—S6—Cu2	115.0 (2)
C1—N2—H2A	120.0	Cu1^ii—S6—Cu2	131.52 (7)
C1—N2—H2B	120.0	N2—C1—N1	119.0 (7)
H2A—N2—H2B	120.0	N2—C1—S1	121.1 (5)
C2—N3—H3A	120.0	N1—C1—S1	119.9 (6)
C2—N3—H3B	120.0	N4—C2—N3	117.9 (6)
H3A—N3—H3B	120.0	N4—C2—S2	121.8 (5)
C2—N4—H4A	120.0	N3—C2—S2	120.2 (5)
C2—N4—H4B	120.0	N5—C3—N6	117.9 (7)
H4A—N4—H4B	120.0	N5—C3—S3	123.7 (6)
C3—N5—H5A	120.0	N6—C3—S3	118.5 (6)
C3—N5—H5B	120.0	N8—C4—N7	118.6 (6)
H5A—N5—H5B	120.0	N8—C4—S4	122.2 (5)
C3—N6—H6A	120.0	N7—C4—S4	119.2 (6)
C3—N6—H6B	120.0	N9—C5—N10	118.6 (8)
H6A—N6—H6B	120.0	N9—C5—S5	124.3 (6)
C4—N7—H7A	120.0	N10—C5—S5	117.1 (7)
C4—N7—H7B	120.0	N11—C6—N12	118.8 (6)
H7A—N7—H7B	120.0	N11—C6—S6	120.3 (5)
C4—N8—H8A	120.0	N12—C6—S6	120.8 (5)
C4—N8—H8B	120.0	N13—C7—C8	178.6 (11)
H8A—N8—H8B	120.0	C7—C8—H8C	109.5
C5—N9—H9A	120.0	C7—C8—H8D	109.5
C5—N9—H9B	120.0	H8C—C8—H8D	109.5
H9A—N9—H9B	120.0	C7—C8—H8E	109.5
C5—N10—H10A	120.0	H8C—C8—H8E	109.5
C5—N10—H10B	120.0	H8D—C8—H8E	109.5
H10A—N10—H10B	120.0

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) x−1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···I2^iii	0.86	2.97	3.799 (7)	161
N1—H1B···S6^i	0.86	2.68	3.524 (7)	167
N2—H2A···I2^iii	0.86	3.14	3.929 (6)	154
N2—H2B···S5	0.86	2.96	3.752 (7)	154
N2—H2B···I1^ii	0.86	3.17	3.667 (7)	119
N3—H3A···I2	0.86	2.87	3.645 (6)	150
N3—H3B···I1^iv	0.86	3.06	3.720 (6)	135
N4—H4A···I2	0.86	3.11	3.837 (7)	144
N4—H4A···I1	0.86	3.22	3.706 (6)	119
N4—H4B···S6^i	0.86	2.73	3.563 (7)	165
N5—H5A···N13^v	0.86	2.41	3.192 (10)	152
N5—H5A···I2^iv	0.86	3.32	3.796 (8)	118
N7—H7A···I1^vi	0.86	3.04	3.839 (7)	156
N7—H7B···I2^iv	0.86	3.02	3.837 (7)	159
N8—H8A···I1^vi	0.86	2.93	3.759 (6)	161
N8—H8B···S5	0.86	2.69	3.526 (6)	166
N9—H9A···I2^vii	0.86	3.12	3.922 (6)	155
N9—H9B···S4	0.86	2.61	3.429 (7)	161
N10—H10A···I1^vii	0.86	3.01	3.716 (7)	141
N11—H11A···I1^viii	0.86	2.99	3.791 (6)	155
N11—H11B···S2^ii	0.86	2.63	3.466 (6)	163
N12—H12A···I1^viii	0.86	2.92	3.732 (6)	158
N12—H12B···S1	0.86	2.54	3.338 (6)	155
N6—H6A···S2^v	0.86	2.89	3.397 (6)	119
N6—H6A···N13^v	0.86	2.51	3.266 (11)	147

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) x−1/2, −y+3/2, −z+1; (iii) x, y+1, z; (iv) x−1/2, −y+1/2, −z+1; (v) −x+1/2, −y+1, z+1/2; (vi) −x+1/2, −y+1, z−1/2; (vii) −x+1, y+1/2, −z+1/2; (viii) −x+1, y+1/2, −z+3/2.